Scott Disick Is Finally Comfortable

The Keeping Up with the Kardashians personality used to be famous for his suits, his lordship, and his foibles. It was a lot. But now he's running a clothing line, raising his kids, and booting up a new reality show—and the business of being Scott Disick is a whole lot more fun.

When you enter the gated confines of the Hidden Hills, California neighborhood where Scott Disick lives, it feels a little like driving onto a Hollywood studio lot left over from the 1930s. There are the hokey street signs bearing the names of once-great actors; the thick woods and gently sloping roads that could provide the setting for a Western; the vertiginous drop into a golden, picturesque valley.

The main difference is all the Range Rovers. There are so many Range Rovers.

Disick’s unlikely reinvention is what brings me to his baronial home on a Thursday afternoon in April. Outside, a Bentley and a Rolls-Royce sulk in the driveway, so ostentatious that they’re almost subtle: it would’ve been far more noteworthy to show up and find a Hyundai. Within the house, the high ceilings and white everything give you a sense of what it must feel like to be inside of an unbroken eggshell. Near the glass doors leading onto the patio, a Greco-Roman statue of a nude man stands, gleaming. In the back, the pool is empty, looking Brutalist and abstract, less a pool than a dream in which a pool appears. The view is so soft and lovely that it makes you want to punch right through a Monet.

Disick, of course, is the 35-year-old, Long Island-born professional famous-person, famous from his decade-plus run as a main character on Keeping Up with the Kardashians—the remarkably inexhaustible reality show that has grown into a powerful mass-media moon, exerting its lunar pull on all the tides of our culture.

But if Disick was once best known as a clownish presence whose sincerity was always in question—whose power suits seemed almost deliberately uncool; whose on-again off-again relationship with Kourtney Kardashian provided the show with an all-too-convenient villain and scapegoat—times have changed.

As we all know, at some point during the last decade, the Kardashians caught up to the culture, or the culture to the Kardashians. Either way, what began as an exploration of fame so dense and self-referential that it was essentially a black hole began to consume and include the world around it, until the two could no longer be separated. As Kylie was scoring Forbes covers and Kim was studying for the bar, Scott pulled off a no-less-unlikely coup d'état: he became a protagonist. And, shortly after that, a budding fashion designer and home-flipper with a show of his own.

Gone is the American Psycho cosplay and constant conflict. In its place is that most endearing, enviable, and mature of qualities, one that seems to increasingly characterize not only his life, but his new lines of work: comfort.

“I think it’s a big F-U to everybody in the world that basically said that anybody that was in the reality business 10, 15 years ago didn’t have talent,” Disick says of why he named his clothing brand Talentless. It’s worth pausing here to note: that’s a really funny name! Nobody had ever been in danger before of confusing Scott Disick with Charlie Kaufman, but you don’t necessarily expect this degree of self-commentary from someone who’s lived his entire adult life in front of a camera.

Speaking of which: as we sit and talk at a massive round table, we’re constantly being strafed by a KUWTK cameraman. In the garage earlier, I’d signed away all rights to my image, my voice, and, quite possibly, my life; I did not read it closely. But in front of the camera’s eye is Disick’s habitat. To speak to him without bearing oneself before it would be insufficient, even disingenuous.

Cameras are just a part of life here in Hidden Hills, like horses and contractors, and Disick’s bearing suggests that he long ago learned how to live with them. When he enters the house, he seems tired, dogged by a nagging cough, but as soon as we sit down and the camera turns on, he goes to work.

As he talks in his slow, high-pitched drawl, he often bangs the table, less for emphasis than accompaniment. He’s the kind of guy whose beard, now that he has one, seems like such an appropriate and essential part of his vibe that seeing pictures of him before it is viscerally upsetting, like looking at a shaved animal. And his blue eyes are really very mesmerizing; as I look at them, I find myself wondering if the Kardashian cast’s collective secret isn’t that they’ve mastered some subtle art of hypnosis.

“I still have friends in New York, and 20 years ago, they were telling me, you couldn’t even go to a business meeting with scruff or a beard: you were not looked at, you were not clean cut,” Disick says. “Now, you’ve got people rolling into offices with beards down to their balls, T-shirts, and they’re tech billionaires.”

Disick’s former resemblance to Patrick Bateman has been so thoroughly exhausted as a concept, serious or comic, that he even shot a send-up of the scene in which Christian Bale takes an axe to Jared Leto, though by then, he’d already grown the beard, which ruined the effect a bit. But these days, he looks more like an off-duty Jake Gyllenhaal than he does a college kid dressing up for Halloween. He looks like what he is, which is a handsome rich guy in LA with a clothing brand.

As office casual took over the world, Disick saw an opportunity to launch the kind of brand that would reflect his new image and lifestyle—and, more importantly, that he could design. The opportunity to put his name on things had never been a hard one to find, and it’s one that he’s taken advantage of, as a quick scroll through his Instagram will reveal. This was different, the opportunity to put his name underneath something.

“You always hear people playing new music and trying to find their way,” he says. “For me, you know, play the hits. I just like to listen to what I know; movies, the same. So for me, I wanted to do what felt normal. I wear sweatshirts, I wear T-shirts, I wear cargo pants, I wear comfortable pants. So I figured, let me make a business, try to make it just as great as anything you see in a high-end department store, but for half the price.”

In the process, he ran into the peculiar nature of pricing clothes: if you make things too cheap, then people don’t want them, because they're cheap; if you make them too expensive, then you’re selling $400 sweatshirts. Disick can afford that, but not all of the people who follow him on Instagram can, nor does he think they should have to. “I think it’s absolutely a mockery how expensive clothing has gotten,” Disick says, sounding impressively sincere for a guy who has a mirrored cradle of suede boots in his closet. “That’s why I wanted to create something that had the same kind of feel, but just some kind of normalcy in price.” (Hoodies run $128; three percent of every Talentless sale goes to the nonprofit Fuck Cancer.)

Resources like Instagram and the whole direct-to-consumer market have allowed Talentless to take off faster than Disick could’ve imagined. And if the type of clothing he makes originated with his own taste, it’s come to be driven by the response he’s finding in the marketplace. Feedback comes in instantly; for example, strong demand from women has pushed what he originally envisioned as a men’s brand toward catering to both sexes.

Regardless, he’s found the transition to be a smooth one. In fact, this moment finds Disick entering into another role as well: he has a new show coming on E!, Flip It Like Disick, that will chronicle his side hustle flipping houses with two of his best friends. Disick is a self-professed architecture nerd who was ogling Italian couches and reading Dwell as a teenager; he’s a big fan of the Hamptons, and can expound on the overexposure of the Gambrel style. When I wonder about the house we’re sitting in now, he admits that it isn’t as modern as he would’ve gone in a vacuum. He wanted his kids to be, you know, comfortable.

I should note here that, by the time I leave Disick’s house, I will have spent more time in front of the KUWTK cameras (about 37 minutes) than actually watching the show (maybe ten, if you include the occasional clip of Kanye). But I’ve still managed to absorb the accomplishments, personalities, and relative arcs of the KUWTK cast, which, like sunlight or radiation, seems to permeate the atmosphere.

This, of course, is life in 2019, in which actually watching a TV show is often the least important aspect of engaging with it; in which having 20 million Instagram followers, as Disick does—@letthelordbewithyou, but you already know that—means you cannot be escaped, least of all by yourself. But Disick hasn’t just defeated the thoroughly obsolete notion of 15 minutes of fame; he’s seen the world remade in his image, and in the process proved what the medium of reality TV can really do.

“People are respected doing reality just as much as any other kind of work,” Disick says. “It used to be the only celebrities were an actor or a singer, and that was it. Right? Now, I think because of all the social media, because of these reality television shows, it’s opened up a different world for a lot of people to make money in all different ways.”

He points to the rise of YouTube stars, Instagram influencers, a whole nation of kids making money off of either the quotidian or the incredibly specific. He helped pioneer this concept, however inadvertently: he demonstrated that one’s talent could be rendering the stuff of their life as spectacle, scene, ready-made narrative. But while the Kardashians have been both castigated and canonized for synthesizing their potent blend of fame, Disick isn’t technically a Kardashian. He’s a member of the family, sure, but a supporting player. He’s had to make his reps count, and coming to terms with this has been a process.

For example: the KUWTK cameras have chronicled plenty of low points, many of them involving alcohol and women who aren’t Kourtney Kardashian. (He and Kardashian never married, and they’ve been separated since 2015.) He’s currently dating Sofia Richie, the 20-year-old daughter of Lionel Richie, which hasn’t exactly been uncontroversial, within the Kardashian universe or the world of its fans. And, uh, he also bought himself an official British knighting ceremony over the Internet, making him an actual lord—a move that implies pretty much the opposite of comfort, though it did show the early potential for self-parody.

Which is to say: he’s doing fine, but being Scott Disick is no walk in the park. Or it is a walk in the park, if 20 million people were watching your feet move. Therein lies the talent. It’s whatever you do that keeps you from losing your mind.

“I think the true talent is just getting used to having to deal with your life being looked at very much like The Truman Show, with a microscope,” Disick says. I may have been under this microscope for only about 40 minutes, but it isn’t hard to understand, even in that short a time, how destabilizing it would be. With the camera watching us, I could feel myself performing the role of GQ interviewer; I could see myself in the monitors, being evaluated for story potential. I gave myself up as clay to the unseen hands of television producers, and I had the uncanny feeling that my body knew this was happening—that it could sense the loss of control.

It was profoundly exhausting, and I had to do it for less than an hour.

“Even though you’re not showing up every day with lines,” he says, “you’re still showing up, and you’re always being looked at, and there’s always people following you, and you know that the life that you’re living is going to relived again a couple months later on national television for everybody to see, comment on. Everywhere you go, people feel as if they know you, and that’s a huge responsibility to take on.”

Television is a zero-sum game, in which whatever part of the frame you take up is a part of the frame that can’t contain someone else. But eventually, Disick learned the lesson that most of us hopefully absorb at some point in our lives, usually with great relief: the key to contentment often lies in the contentedness of those around you.

“Unfortunately, I had to lose my parents at a pretty early age, and I think it took a minute for me to understand that I surely don’t want to lose anybody else that I love, especially while they’re living,” Disick says. “In order to keep these people, I’ve got to treat people the way I want to be treated. I know that I can make people happy, and, over time, I’ve started to make people happy, and everything has come together after that, and things have fallen into place for me.”

This includes, especially, his kids. There are three of them—Mason, Penelope, and Reign. They make regular appearances on Disick’s Instagram, which is basically a paean to his children and his clothes. (Put together, the two naturally connect: there are few greater scholars of comfort than dads. Just ask fellow Kardashian satellite Kanye West, whose Yeezy influence can be seen in Talentless’s dusty sweats.) The kids bring comfort with them, shrinking the world down into the size of wherever they are.

For a guy whose world had previously been spread among tens of millions of people, you can imagine how potent that shift might be. And in our time together, he comes off like a guy glad to be emerging from years spent trying to entertain at all costs. Plenty of people, men especially, are moved to live like this in their younger lives, though most don’t have an audience of millions, demanding that they give a good performance. Disick may have been an enfant terrible within the KUWTK universe, a bad-boy counterweight, but he never seemed like he was enjoying it all that much.

Therein might lie the secret to the mystery of Scott Disick, the key to how he became a character worth rooting for, not only on TV, but in his own life: he finally figured out what game he was playing.

“It’s cool for fathers now that they’re so much more involved in their children’s lives, where it used to just be the guy works, that’s it, they see their kids when they get home from work, they kiss them goodnight, and that’s it,” he says. “My kids are literally my best friends, and I try to see them every second that I have of the day. That’s what I do it for.”

As Disick prepared to film a video in front of yet another set of cameras, I headed out into the Valley heat, relieved to step off the set. That the set was Disick’s life inspired a strange feeling in me: sympathy. God knows Scott Disick doesn’t need my sympathy, but that didn’t make me any less glad that he’d managed to find comfort in his life—and his sweatpants.